This is the first of a series of posts this week on careers in innovation and startups--sort of a thought exercise for me on the topic for my talk at General Assembly at 8PM on 12/15.

With any company I work with, I inevitably play the role or recruiter--mostly because I often play the role of career counselor to friends and other folks in the community. I've been thinking about career paths for a long time. I even started a company around helping people figure out how to get from A to B, because information in this area is so poor. People have no idea what their options are, nor where those options can take them.

In the world of startups and innovation, it's even less clear. Should I take the low level biz dev job at Amazon or the lead biz dev role for an unfunded, three person startup? Associate position at a top tier VC fund or lead dog for a random pool of high net worth money that no one's ever heard of?

When you work at Chase or PWC, your career trajectory is more established--you go from Assistant Trader to Trader to Trading Manager to Director of Trading to VP and so on. In the startup world, with companies of varying sizes, hypergrowth potential, and job titles that don't exactly encompass what you do, it's not exactly obvious to figure out how to navigate this.

What it comes down to is a series of tradeoffs--variables that you will try to optimize for but that there's no way you're going to be able to maximize every one. It just depends on what's most important to you, what your risk tolerances are, etc.

The benefits, however, are tremendous. Working at a high growth company can often jump start your career because you can get a high-responsibility job you otherwise wouldn't be qualified for in a more established company--and if you rock it, you can skip several rungs on the corporate ladder. That's to say nothing of work environment or potential for economic outcome if a company becomes successful.

Here are some of the tradeoffs when jumping into the startup world or choosing your next job:

Certainty of Company Outcome

It's pretty obvious that Square is going to be a successful company. They have lots of revenues, high growth, funding, etc. Because of that, you're simply not going to get a major chunk of equity, nor are you going to get hired there without a ton of relevant experience. At a three person startup that isn't funded yet, you'll get a ton of responsibility, but it's not clear how successful things are going to be. What I've found is that the benefit of being at a "name brand" successful startup like a Square, Zynga, Twitter, etc. is when you have a position that you only could have gotten before the outcome became so certain. If you spent the last year in a business development job at Twitter, it's fine--certainly better than working at Chase, but you didn't take a lot of risk, and Twitter was kind of big already when you started. You probably didn't have that much time getting meetings and you probably got paid a pretty normal salary. It's a good job, but it isn't going to rocket you up to the top of the resume pile nearly as much as being super early to a company that has been successful, where you took risks, built a biz dev team when there wasn't one, struck an early deal when no one had ever heard of the company, etc.

Of course, the flip side of taking the three person startup risk is that, if it fails, is that going to look bad? I'd say no--as long as that doesn't become your pattern. If you have a long string of three to six month roles at companies that never really get off the ground or at least get into orbit with some funding, your next company is going to wonder if you're just not a winner. People might think that top tier teams that build top tier companies have passed you over, or you're not necessarily someone who can evaluate and pick top talent to surround yourself with--fair or not. That's why people often take the portfolio approach when managing their career. If they take a big risk on a small team, and it flames out, they might take that Twitter job next, just to get some stability and a solid name in the mix before taking another big risk. It's often why acq-hires aren't necessarily the worst thing for your career--especially if you manage to make an impact at your new company.

The Role You Want vs The Role You Get

A lot of times, the roles that are open to non-founders at companies aren't necessarily the ones they wanted. You might never have done marketing or product before, but a team likes you and wants you to be a product marketing person. This happens a lot because startups tend to hire for character over and above a specific set of experience on your resume.

There are a lot of plusses and minuses here. On the plus side, it's better to be at a company you like that has a good chance of success--especially if you can get an early role--than being at a big company that is killing your soul.

On the other hand, it's problematic if you get hired to do one job, but you really have your eye on something else. You become distracted at the job at hand, and perhaps even resentful that you're not doing something else. The one thing you never want to do is to fail at the job at hand because you took your eye off the ball. On top of that, the more work experience you have in a certain area, the more typecast you are going to get. One or two marketing jobs is all someone needs to basically only consider you for marketing jobs. Same with sales and business development--two "starter" areas where good people jump into first just to get their startup feet wet, but that don't necessarily brand people as ready for something else. If I wanted to be a product design person, just doing biz dev at a startup isn't going to help me get a product design job in the future, even though I've "proven" that I can work at a startup. I'd need something else, because I'm competing against someone who did product design at a big company--and it's easier to prove character than it is to prove skill. You can get someone to like you after one interview, but it's tough to convince someone you can lead product design after you've been doing sales for five years. I'd try to be patient here to find the job you want--or work really hard to build up the skillset necessarily to be qualified for it.

Doing Your Own Thing vs Joining Someone Else's

I think a lot of people are in love with the idea of being an entreprenuer, but they don't actually want to start a company. Starting a company is ridiculously hard and it requires not just a kick-ass idea, but a serious dedication (obsession) to a space. If you're going to start the next daily-deal site, you better eat, sleep, breathe deals, ecommerce, and customer acquisition, because that's what it's going to take to be successful. We have incubators, accellorators, hackathons, Startup Weekends, etc all designed to get more people starting things--as if starting is somehow better than joining. We say it's better to be a leader than a follower, but 1) not everyone is good at leadership and 2) if we were all leaders, we'd never get anything done.

I find that someone of the most thoughtful, qualified people I know have attempted something on their own and failed at it. People may worry about what job comes from "Failed Startup CEO", but I think others will tell you that it doesn't look bad at all. If anything, lots of people who got to see how you worked when you were on your own are more than willing to reach out when you're looking for your next thing after you've fallen down. It qualifies you to do a wide variety of things--to focus on any of the areas that you didn't get enough resources to concentrate on when you were CEO.

So, when someone tells me they want to get something out of their system, I'm all for it--if they can manage risk around it. Prove something to yourself about your potential for success before you raise enough money to get stuck in the idea for two years. Launch, sell a customer, or de-risk something important, because, in this environment, your biggest cost is opportunity cost.

At the same time, I think the best experience you can have before being an entrepreneur is being a part of a successful team. You get to see what winning ways look like--what worked and what didn't--and you have access to better networks of talent and capital to do your next thing with. That's one of the reasons why I do events and talks around building up "bench talent"--the marketing folks, design leads, etc., because the more people who join startups as team players, the more startups we're going to have in a few years led by experience people who know what it takes to grow something big.

What other tradeoffs have you had to think about in your career around innovative companies and startups?